10 Memorable Road‑Trip Vacations Within Two Hours of Boston

Here are ten amazing places you can drive to within two hours of Boston—ready for family fun, seaside breezes, or island-style relaxation.

1. Newport, Rhode Island (~1.5 hours)

Explore the famous Cliff Walk, stroll past Gilded Age mansions, and enjoy upscale seafood waterside. Take a harbor cruise or rent bikes to ride along the historic coast. 

2. Portland, Maine (~2 hours)

The Old Port district is a foodie paradise with dazzling boutiques and craft beer bars. Visit Portland Head Light and savor fresh lobster at local harborside shacks. 

3. Hampton Beach, New Hampshire (~1.5 hours)

A classic seaside town with boardwalk arcades, sandy beaches, and summer concerts. Try local clam chowder and watch fireworks above the waves.

4. Nantucket, Massachusetts (~2 hours drive + ferry)

Drive to Hyannis, hop a ferry, and enjoy this charming island. Look for Brant Point Lighthouse, stroll the Sconset Bluff Walk, or visit the Whaling Museum. 

5. Martha’s Vineyard, Massachusetts (~2 ¼ hours)

From Boston it’s about 89 miles (143 km), roughly 2½ hours drive including ferry time. Visit Oak Bluffs, enjoy beaches, and explore art galleries in Edgartown. 

6. Mystic, Connecticut (~2 hours)

Mystic is a coastal gem—home to the Mystic Seaport Museum, the largest maritime museum in the U.S., receiving around 250,000 visitors annually. And don’t miss Mystic Aquarium, with the only beluga whales in New England and over 10,000 animals. Other activities: walk Olde Mistick Village, take a boat cruise on the schooner Argia or steamer Sabino, or drive to nearby Stonington Borough to stroll the harbor shops.

7. Cape Cod (Provincetown or Hyannis) (~1½–2 hours)

Drive down to Hyannis or farther to Provincetown at the Cape’s tip. Enjoy dunes, beaches, seafood—plus the vibrant town of P‑town.

8. Salem, Massachusetts (~45 minutes)

Famous for the Witch Trials, Salem attracts over a million tourists each October. Visit the Witch House, Peabody Essex Museum, themed tours, and historic sites year‑round. 

9. Scarborough / Old Orchard Beach, Maine (~2 hours)

Classic Maine beach town just around 96 miles north of Boston. Visit Portland Head Light, walk sandy beaches, and hit local seafood joints. 

10. Berkshires (western Massachusetts) (~2 hours)

Though a bit inland, the Berkshires offer leafy drives, art museums (like MASS MoCA), Edith Wharton’s Mount, and Tanglewood concerts. Beautiful especially in October leaf-peeping season. 

Why These Destinations Work for Drive‑time Vacations

• All are about 120 miles or less from Boston—or about two hours in normal traffic.

• They offer variety—coastal towns, islands, historic museums, beaches, food, and culture.

• Many include interactive, kid‑friendly or scenic experiences that everyone enjoys.

  
  

How We Can Help You Plan

At www.getvacationhigh.com, we specialize in designing short road‑trip getaways that are easy to book and fun to explore. From day‑trip itineraries to overnight stays with recommendations for activities and places to eat, we make planning stress-free—so you can focus on making vacation memories.

So pack your bags, fill the tank—and pick one of these destinations to explore next weekend. Which one will you visit first?